ORGN 653 |
Studies towards the synthesis of the BCDEF ring system of Penitrem D
| Felix Gonzalez-Lopez de Turiso1, Alexey Rivkin2, and Dennis Curran1. (1) Department of Chemistry, University of Pittsburgh, Chevron Science Center. Room 1114, 219 Parkman Avenue, Pittsburgh, PA 15260, (2) Sloan-Kettering Institute, 1275 York Avenue, New York, NY 10021 |
| Alkylation reactions between benzyl bromides 1 and cyclobutane 2 were the key steps in the synthesis of a number of tethered cyclobutene precursors, 3. These substrates underwent facile intramolecular cyclization under different conditions providing access to a number of disubstituted and trisubstituted cyclobutanes, 4. Application of this alkylation strategy to the more functionalize aromatic ring 5 produced the desired precursor 7 that underwent chemoselective intramolecular cyclization under Pd-catalyzed conditions. The resulting intermediate 8 shows the necessary functionality for its transformation into the BCDEF ring core structure of Penitrem D, 9. 
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New Reactions, Methodology, Heterocycles, Aromatics
8:00 PM-10:00 PM, Wednesday, August 25, 2004 Pennsylvania Convention Center -- Hall D, Poster
Division of Organic Chemistry
The 228th ACS National Meeting, in Philadelphia, PA, August 22-26, 2004
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